Extended pi-Conjugated Molecules Derived from Naphthalene Diimides toward Organic Emissive and Semiconducting Materials

doi:10.1021/jo302677k

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	Extended pi-Conjugated Molecules Derived from Naphthalene Diimides toward Organic Emissive and Semiconducting Materials
	Li, Yonghai ; Zhang, Guanxin 1; Yang, Ge ; Guo, Yunlong ; Di, Chong'an ; Chen, Xin ; Liu, Zitong ; Liu, Huiying ; Xu, Zhenzhen ; Xu, Wei
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2013-04-05
卷号	78 期号:7 页码:2926-2934
ISSN号	0022-3263
DOI	10.1021/jo302677k
英文摘要	In this paper, a new synthetic way to modify naphthalene diimide (NDI) at "shoulder" positions is reported. The key step of the transformation is the intramolecular cyclization involving ethynyl and imidecarbonyl groups. The structure of the intermediate pyrylium cation was confirmed by X-ray crystal structural analysis. New conjugated molecules 1a-g were successfully synthesized in acceptable yields. Their absorption and fluorescence spectra were measured. Among them 1c-f are strongly emissive in solutions. Furthermore, 1b-f are also fluorescent in their solid states; in particular, 1b exhibits a typical aggregation-induced enhanced emission feature. Yellow-emissive microfibrils of Id show potential optical waveguide behavior. HOMO/LUMO energies of 1a-f were determined based on their cyclic voltammograms. The results also reveal that HOMO/LUMO energies of these new conjugated molecules are influenced by the two flanking moieties. Notably, the thin film of 1c that is emissive shows p-type semiconducting behavior with hole mobility up to 0.0063 cm(2) V-1 s(-1) based on the transfer and output characteristics of the OFET (organic field effect transistor).
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000317327800011
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/54071]
专题	中国科学院化学研究所
通讯作者	Zhang, Guanxin
作者单位	1.Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, Organ Solids Lab, Beijing 100190, Peoples R China 2.Chinese Acad Sci, Inst Chem, Photochem Lab, Beijing 100190, Peoples R China
推荐引用方式 GB/T 7714	Li, Yonghai,Zhang, Guanxin,Yang, Ge,et al. Extended pi-Conjugated Molecules Derived from Naphthalene Diimides toward Organic Emissive and Semiconducting Materials[J]. JOURNAL OF ORGANIC CHEMISTRY,2013,78(7):2926-2934.
APA	Li, Yonghai.,Zhang, Guanxin.,Yang, Ge.,Guo, Yunlong.,Di, Chong'an.,...&Zhang, Deqing.(2013).Extended pi-Conjugated Molecules Derived from Naphthalene Diimides toward Organic Emissive and Semiconducting Materials.JOURNAL OF ORGANIC CHEMISTRY,78(7),2926-2934.
MLA	Li, Yonghai,et al."Extended pi-Conjugated Molecules Derived from Naphthalene Diimides toward Organic Emissive and Semiconducting Materials".JOURNAL OF ORGANIC CHEMISTRY 78.7(2013):2926-2934.